After a semester of study at Black Mountain College in North Carolina, Cy Twombly, poet and sculptor as well as a painter, settled in Rome, Italy, where he joined a group of calligraphic painters. He was inspired by the gestural spontaneity of Robert Motherwell and Franz Kline, but instead of their soul-to-hand connections, he developed an intellect-to-hand connection in his work. Twombly's "writings" are the result of a calligraphic style of configuring of letters, words, and images in an "anti-compositional" order of random graffiti. Deliberately avoiding the individual gesture of Abstract Expressionism, Twombly's work originates from the anonymity of graffiti.

In contrast to the aggressively autographic lines in the abstractions of Jackson Pollock and Willem deKooning, Twombly's lines are sensitive and ambiguous. In diminishing the importance of individual identity, his work is closer in purpose to that of Jasper Johns and John Cage. Like them he often makes allusions to mythological themes and cultural traditions influential in art historical development. Ritratto d'Artista can be translated as "Portrait of the Artist" or as "Portraying the Artist," but Twombly places this work in the broader context of Italian Renaissance portraiture. Most sixteenth-century Italian portraits were either faithful renditions of the external visual characteristics, or idealized versions of the physical imperfections of the subject and were considered as less important than history paintings. However, some portraits by Raphael and Titian represented the personalities of their subjects, thereby adding a component to portraiture, establishing it as a fully recognized art form with its own standards. Twombly's work emanates from this artistic tradition, but his self-portrait is "written" in the visual language of abstraction, inviting an intellectual response that connects with memory associations.